Many of the temples are said to have been founded or restored by the revered monk and scholar Kūkai (空海), better known by his posthumous title Kōbō Daishi (弘法大師). Among his many achievements, he is said to have created the kana syllabary, brought the tantric teachings of Esoteric Buddhism from China, developed it into the uniquely Japanese Shingon sect, and founded Shingon's headquarters on Mount Koya near Osaka.

While most modern-day pilgrims (an estimated 100,000 yearly) travel by tour bus, a small minority still set out the old-fashioned way on foot, a journey which takes about six weeks to complete. Pilgrims, known as o-henro-san (お遍路さん), can be spotted in the temples and roadsides of Shikoku clad in a white jacket emblazoned with the characters Dōgyō Ninin (同行二人), meaning "two traveling together" — the other traveler being the spirit of Kobo Daishi.

Locals will be excited to see someone making the journey on foot, and priests will be relieved that you are not showing up with 100 of your close friends. Make sure that your Japanese is good enough to communicate your feelings to both groups!

Completing the course the traditional way on foot is a serious undertaking that demands several weeks. Good physical fitness and stamina are required to endure the stress of constant walking up and down the hills of Shikoku, in the burning sun and the pouring rain.

Many pilgrims choose to dress up in traditional attire:

byakue — the white coat of a pilgrim

wagesa — scarf worn around the neck, usually purple, to indicate that you are on a religious pilgrimage

sugegasa — conical straw hat

kongōtsue — walking stick, and the one indispensable sign that identifies you as a pilgrim

In addition, most pilgrims carry a book called nōkyōchō or shuincho, to collect red ink stamp (shu-in) by each temple you visit. All of these items can be purchased -in a formal sense- at Mount Koya or at Ryozenji, the first temple.

It should be noted that many pilgrims who begin the pilgrimage on foot do not finish it. It is a common to hear of people giving up in Kochi, traditionally known as "devil's land" because of its hot temperature, intense rain, and infrequent contact with civilization. (This means you must either camp, sleep in a rest stop or precisely time your journey to only hit towns and be willing to pay up for a hotel room.)

It is traditional to prepare by visiting Mount Koya, but the route itself starts at Ryōzenji, near Tokushima, and you have to return here in order to complete your pilgrimage. It is not necessary to start at temple #1 as long as you visit them all, but this is by far the most popular starting point for pilgrims from outside Shikoku, because it is also the closest to people coming from Mt. Koya.

The temples are usually visited in clockwise order, although this too, is just a convention — in practice, as all signs are oriented for pilgrims going clockwise, it's easier to get lost if you try to go against the flow.

There are many small inns that cater to pilgrims traveling either by foot or car. They typically cost between ¥4000-7000 per night, including dinner.

Most temples provide lodging for henro, but it can be quite expensive (around ¥8000 per night is average).

"Henro houses" are run by families or local businesses, and offer rooms (and sometimes food) to walking henro for a very small fee — or sometimes for free.

There are also small free lodgings called zenkonyado and tsuyado that lodge travelers for the night, although these lodgings can be somewhat poor quality and have very limited facilities. (There is a zenkonyado near Zentsuji which is said to be haunted.) These were once the primary lodgings for walking henro; however, the island's culture has changed in the last 50 years, and the number of these lodgings have been reduced to just a handful.

Traveling in Shikoku is very safe, especially when you wear the traditional henro robes. People will be very helpful if they recognize you as a pilgrim, and will try to participate in your journey by giving you small gifts (osettai), which you must always accept.

The weather can be perilous at times; even during the optimal seasons of spring and fall, it may rain for days — particularly in the south. Proper preparation and staying up to date with weather reports is a must. You are, however, never far from civilization in case of emergency.

Be careful while walking in Kochi Prefecture, as it is the least populated. The major towns are far apart, and the coast is lined with small fishing towns that tend to shut down by eight or nine in the evening, making it difficult to find accommodations.

Shikoku is home to many snakes, including deadly pit vipers. When walking through brush or grass, stomping or otherwise making noise will divert most snakes from your path.

July and August are very hot, and attempting to walk the pilgrimage at the peak of summer is asking for a bad case of heatstroke. But for the brave, it can mean small crowds and almost guaranteed space at the henro houses. April and October are the best times to go, though accommodations will be particularly crowded.

You aren't done when you reach the 88th temple — you still have to trek back to the 1st to officially complete your pilgrimage! And if you've made it this far, it's only good manners to return to Mount Koya to give your thanks to Kobo Daishi.